Therapeutic applications of synthetic retinoids

IDrugs

Volumn 3, Issue 1, 2000, Pages 73-83

  Kagechika, Hiroyuki ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002116509     PISSN: 13697056     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (128)

1. The Retinoids. Sporn MB, Roberts AB, Goodman DS: (Eds) 2nd Edition, Raven Press, New York 1994.
2. Retinoid Therapy Cunliffe WJ, Miller AJ: (Eds) MTP Press Limited, Lancaster, 1984.
3. Bollag W, Holdener EE: Retinoids in cancer prevention and therapy. Ann Oncol (1992) 3(7):513-526.
4. Hill DL, Grubbs CJ: Retinoids and cancer prevention. Ann Rev Nutr (1992) 12:161-181.
5. IUPAC-IUB Joint Commition on Biochemical Nomenclature, Nomenclature of retinoids Recommendation 1981. Eur J Biochem (1982) 129:1-5.
6. Sporn MB, Robert AB: Retinoids, differentiation and diseases. Introduction: What is a retinoid? Ciba Found Symp (1985) 113:1-5.
7. Sporn MB, Roberts AB, Roche NS, Kagechika H, Shudo K: Mechanism of action of retinoids. J Am Acad Dermatol (1986) 15:756-764.
8. Petkovich M, Brand NJ, Krust A, Chambon P: A human retinoic acid receptor which belongs to the family of nuclear receptors. Nature (1987) 330(6147):444-450.
9. Giguere V, Ong ES, Segui P, Evans RM: Identification of a receptor for the morphogen retinoic acid. Nature (1987) 330(6149):624-629.
10. Chambon P: A decade of molecular biology of retinoic acid receptors. FASEB J (1996) 10:940-954.
11. Gronemeyer H, Laudet V: Nuclear receptors. Protein Profile (1995) 2:1173-1308.
12. Mangelsdorf DJ, Thummel C, Beato M, Herrlich P, Schuetz G, Umesono K, Blumberg B, Kastner P, Mark M, Chambon P, Evans RM: The nuclear receptor superfamily: the second decade. Cell (1995) 83:835-839.
13. Heyman RA, Mangelsdorf DJ, Dyck JA, Stein RB, Eichele G, Evans RM, Thaller C: 9-Cis retinoic acid is a high affinity ligand for the retinoid X receptor. Cell (1992) 68(2):397-406.
14. Zhang X-K, Lehmann J, Hoffmann B, Dawson MI, Cameron J, Graupner G, Hermann T, Tran P, Pfhl, M: Homodimer formation of retinoid X receptor induced by 9-cis retinoic acid. Nature (1992) 358(6387):587-591.
15. Shudo K, Kagechika H: Structural evolution of retinoids. Adv Drug Res (1993) 24:81-119.
16. Curley Jr RW, Robarge MJ: Recent advances in the development of retinoids. Curr Med Chem (1996) 3:325-342.
17. Forman M, Umesono K, Chen J, Evans RM: Unique response pathways are established by allosteric interactions among nuclear hormone receptors. Cell (1995) 81:541-550.
18. Kurokawa R, Söderström M, Hörlein A, Halachmi S, Brown M, Rosenfeld MG, Glass CK: Polarity-specific activities of retinoic acid receptors determined by a co-repressor. Nature (1995) 377(6548):451-454.
19. Vivat V, Zechel C, Wurtz J-M, Bourguet W, Kagechika H, Umemiya H, Shudo K, Moras D, Gronemeyer H, Chambon P: A mutation mimicking the ligand-induced transconformation yields a constitutive RXR that senses allosteric effects in heterodimers. EMBO J (1997) 16(18):5697-5709.
20. Leblanc BP, Stunnenberg HG: 9-Cis retinoic acid signaling: changing partners causes some excitement. Genes Dev (1995) 9:1811-1816.
21. Mukherjee R, Jow L, Croston GE, Patemiti Jr, JR: Identification, characterization, and tissue distribution of human peroxisome proliferator-activated receptor (PPAR) isoforms PPARγ2 versus PPARγ1 and activation with retinoid X receptor agonists and antagonists. J Biol Chem (1997) 272(21):8071-8076.
22. Mukherjee R, Davies PJA, Crombie DL, Bischoff ED, Cesario RM, Jow L, Hamann LG, Boehm MF, Mondon CE, Nadzan AM, Patemiti Jr JR, Heyman RA: Sensitization of diabetic and obese mice to insulin by retinoid X receptor agonists. Nature (1997) 386(6623):407-410.
23. Mayer H, Bollag W, Hanni R, Ruegg R: Retinoids, a new class of compounds with prophylactic and therapeutic activities In oncology and dermatology. Experientia (1978) 34:1105-1119.
24. Ellis CN, Voorhees JJ: Etretinate therapy. J Am Acad Dermatol (1987) 16(2 Part 1):267-291.
25. Fritsch PO: Retinoids in psoriasis and disorders of keratinization. J Am Acad Dermatol (1992) 27(6 Part 2):S8-S14.
26. Muto Y, Moriwaki H, Omori M: In vitro binding affinity of novel synthetic polyprenoids (polyprenoic acids) to cellular retinoid-binding proteins. GANN (1981) 72(6):974-977.
27. Araki H, Shidoji Y, Yamada Y, Moriwaki H, Muto Y: Retinoid agonist activities of synthetic geranyl geranoic acid derivatives. Biochem Biophys Res Commun (1995) 209:66-72.
28. Kagechika H, Kawachi E, Hashimoto Y, Himi T, Shudo K: Retinobenzoic acids. 1. Structure-activity relationships of aromatic amides with retinoidal activity. J Med Chem (1988) 31(11):2182-2192.
29. Tobita T, Takeshita A, Kitamura K, Ohnishi K, Yanagi M, Hiraoka A, Karasuno T, Takeuchi M, Miyawaki S, Ueda R, Naoe T, Ohno R: Treatment with a new synthetic retinoid, Am-80, of acute promyelocytic leukemia relapsed from complete remission induced by all-trans retinoic acid. Blood (1997) 90(3):967-973.
30. Kagechika, H Kawachi E, Hashimoto Y, Shudo K: Retinobenzoic acids. 2. Structure-activity relationships of chalcone-4-carboxylic acids and flavone-4′-carboxylic acids. J Med Chem (1989) 32(4):834-840.
31. Jetten AM, Anderson K, Deas MA, Kagechika H, Lotan R, Rearick JI, Shudo K: New benzoic acid derivatives with retinoid activity: Lack of direct correlation between biological activity and binding to cellular retinoic acid binding protein. Cancer Res (1987) 47(13):3523-3527.
32. Rees JL, Daly AK, Redfern CPF: Differential expression of the α and β retinoic acid receptors in tissues of the rat. Biochem J (1989) 259(3):917-919.
33. Elder JT, Fisher GJ, Zhang Q-Y, Eisen D, Krust A, Kastner P, Chambon P, Voorhees JJ: Retinoic acid receptor gene expression in human skin. J Invest Dermatol (1991) 96:425-433.
34. Hashimoto Y, Kagechika H, Shudo K: Expression of retinoic acid receptor genes and the ligand-binding selectivity of retinoic acid receptors (RARs). Biochem Biophys Res Commun (1990) 166:1300-1307.
35. Delescluse C, Cavey MT, Martin B, Bernard BA, Reichert U, Maignan J, Darmon M, Shroot B: Selective high affinity retinoic acid receptor α or β-γ ligands. Mol Pharmacol (1991) 40:556-562.
36. Crettaz M, Baron A, Siegenthaler G, Hunziker W: Ligand specificities of recombinant retinoic acid receptors RARα and RARβ Biochem J (1990) 272(2):391-397.
37. Fukasawa H, Iijima T, Kagechika H, Hashimoto Y, Shudo K: Expression of the ligand-binding domain-containing region of retinoic acid receptors α, β and γ in Escherichia coli and evaluation of ligand-binding selectivity. Biol Pharm Bull (1993) 16:343-348.
38. Yamakawa T, Kagechika H, Kawachi E, Hashimoto Y, Shudo K: Retinobenzoic acids. 5. Retinoidal activities of compounds having a trimethylsilyl or trimethylgermyl group(s) in human promyelocytic leukemia cells HL-60. J Med Chem (1990) 33(5):1430-1437.
39. Hashimoto Y, Kagechika H, Kawachi E, Fukasawa H, Saito G, Shudo K: Evaluation of differentiation-inducing activity of retinoids on human leukemia cell lines HL-60 and NB4. Biol Pharm Bull (1996) 19(10):1322-1328.
40. Teng M, Duong TT, Klein ES, Pino ME, Chandraratna RAS: Identification of a retinoic acid receptor α subtype specific agonist. J Med Chem (1996) 39(16):3035-3038.
41. Chandraratna RSA, Henry E, Attard J, Gillett SJ, Song T, Garst ME, Nagpal S, Athanikar J, Arefieg T, Gil DW, Wheeler LA, Lew-Kaya D, Sefton J: Development of RAR subtype selective retinoids for dermatological diseases. Eur J Med Chem (1995) 30:506s-517s.
42. Krueger GG, Drake LA, Elias PM, Lowe NJ, Guzzo C, Weinstein GD, Lew-Kaya DA, Lue JC, Sefton J, Chandraratna RSA: The safety and efficacy of tazarotene gel, a topical acetylenic retinoid, in the treatment of psoriasis. Arch Dermatol (1998) 134(1):57-60.
43. Johnson AT, Klein ES, Wang L, Pino ME, Chandraratna RAS: Identification of retinoic acid receptor β subtype specific agonists. J Med Chem (1996) 39(26):5027-5030.
44. Bernard BA, Bernardon J-M, Delescluse C, Martin B, Lenoir M-C, Maignan J, Charpentier B, Pilgrim WR, Reichert U, Shroot B: Identification of synthetic retinoids with selectivity for human nuclear retinoic acid receptor ̃. Biochem Biophys Res Comm (1992) 186(2):977-983.
45. Charpentier B, Bernardon J-M, Eustache J, Millois C, Martin B, Michel S, Shroot B: Synthesis, structure-affinity relationships, and biological activities of ligands binding to retinoic acid receptor subtypes. J Med Chem (1995) 38:4993-5006.
46. Chen JY, Clifford J, Zusi C, Starrett J, Tortolani D, Ostrowski J, Reczek PR, Chambon P, Gronemeyer H: Two distinct actions of retinoid-receptor ligands. Nature (1996) 382(6594):819-822.
47. Weiss JS, Shavin JS: Adapalene for the treatment of acne vulgaris. J Am Acad Dermatol (1998) 39:S50-S54.
48. Renaud J-P, Rochel N, Ruff M, Vivat V, Chambon P, Gronemeyer H, Moras D: Crystal structure of the RAR-γ ligand-binding domain bound to all-trans retinoic acid. Nature (1995) 378(6558):681-689.
49. Bourguet W, Ruff M, Chambon P, Gronemeyer H, Moras D: Crystal structure of the ligand-binding domain of the human nuclear receptor RXR-α. Nature (1995) 375(6530):377-382.
50. Wurtz J-M, Bourguet W, Renaud J-P, Vivat V, Chambon P, Moras D, Gronemeyer H: A canonical structure for the ligand-binding domain of nuclear receptors. Nature Struct Biol (1996) 3(2):87-94.
51. Klaholz BP, Renaud J-P, Mitschler A, Zusi C, Chambon P, Gronemeyer H, Moras D: Conformational adaptation of agonists to the human nuclear receptor RARγ. Nature Struct Biol (1998) 5(3):199-202.
52. Saurat J-H: Oral isotretinoin. Where now, where next? Dermatology (1997) 195(Suppl 1):1-3.
53. Gollnick H, Schramm M: Topical drug treatment in acne. Dermatology (1998) 196:119-125.
54. Michel S, Jomard A, Démarchez M: Pharmacology of adapalene. Br J Dermatol (1998) 139(Suppl 52):3-7.
55. DiSepio D, Chandraratna RSA, Nagpal S: Novel approaches for the treatment of psoriasis. Drug Disc Today (1999) 4:222-231.
56. Federman DG, Froelich CW, Kirsner RS: Topical psoriasis therapy. Am Fam Phys (1999) 59:957-962.
57. Nesher G, Zuckner J: Rheumatologic complications of vitamin A and retinoids. Semin Arthritis Rheum (1995) 24:291-296.
58. Sturkenboom MCJM, Dejong-van der Berg LTW, van Voorst-Vader PC, Cornel MC, Stricker BHCH, Wesseling H: Inability to detect plasma etretinate and acitretin is a poor predictor of the absence of these teratogens in tissue after stopping acitretin treatment. Br J Clin Pharm (1994) 38:229-235.
59. Orfanos CE, Ehlert R, Gollnick H: The retinoids. A review of their clinical pharmacology and therapeutic use. Drugs (1987) 34(4):459-503.
60. Ishibashi Y: Clinical effect of Am-80 ointment on psoriasis and pustulosis palmaris et plantaris (phase III study). Rinsho Iyaku (1995) 11:747-759.
61. Lebwohl M, Poulin Y: Tazarotene in combination with topical corticosteroids. J Am Acad Dermatol (1998) 39:s139-s143.
62. Lebwohl MG, Breneman DL, Goffe BS, Grossman JR, Ling MR, Milbauer J, Pincus SH, Sibbald RG, Swinyer LJ, Weinstein GD, Lew-Kaya DA, Lue JC, Gibson JR, Sefton J: Tazarotene 0.1% gel plus corticosteroid cream in the treatment of plaque psoriasis. J Am Acad Dermatol (1998) 39:590-596.
63. Hong WK, Sporn MB: Recent advances in chemoprevention of cancer. Science (1997) 278:1073-1077.
64. Hong WK, Lippman SM, Itri LM, Karp DD, Lee JS, Byers RM, Schantz SP, Kramer AM, Lotan R, Peters LJ, Dimery IW, Brown BW, Goepfert H: Prevention of second primary tumors with isotretinoin in squamous-cell carcinoma of the head and neck. New Engl J Med (1990) 323(12):795-801.
65. Pastorino U, Infante M, Maioli M, Chiesa G, Buyse M, Firket P, Rosmentz N, Clerici M, Soresi E, Valente M: Adjuvant treatment of stage I lung cancer with high-dose vitamin A. J Clin Oncol (1993) 11:1216-22.
66. Costa A, De Palo G, Decensi A, Formelli F, Chiesa F, Nava M, Camerini T, Marubini E, Veronesi U: Retinoids in cancer chemoprevention. Clinical trials with the synthetic analogue fenretinide. Ann NY Acad Sci (1995) 768:148-62.
67. Muto Y, Moriwaki H, Ninomiya M, Adachi S, Saito A, Takasaki KT, Tanaka T, Tsurumi K, Okuno M, Tomita E, Nakamura T, Kojima T: Prevention of second primary tumors by an acyclic retinoid, polyprenoic acid, in patients with hepatocellular carcinoma. New Engl J Med (1996) 334(24) 1561-1567.
68. Muto Y, Moriwaki H, Saito A: Prevention of second primary tumors by an acyclic retinoid in patients with hematocellular carcinoma. New Engl J Med (1999) 340:(13)1046-1047.
69. Breitman TR, Selonick SE, Collins SJ: Induction of differentiation of the human promyelocytic leukemia cell line (HL-60) by retinoic acid. Proc Natl Acad Sci USA (1980) 77(5):2936-2940.
70. Honma Y, Takenaga K, Kasukabe T, Hozumi M: Induction of differentiation of cultured human promyelocytic leukemia cells by retinoids. Biochem Biophys Res Comm (1980) 95(2):507-512.
71. Koeffler HP, Heitjan D, Mertelsman R, Kolitz JE, Schulman P, Itri L, Gunter P, Besa E: Randomized study of 13-cis retinoic acid v placebo in the myelodysplastic disorders. Blood (1988) 71(3):703-708.
72. Huang M, Ye Y, Chen S, Chai J, Lu J, Zhoa L, Gu L, Wang Z: Use of all-trans retinoic acid in the treatment of acute promyelocytic leukemia. Blood (1988) 72(2):567-572.
73. Castaigne S, Chomienne C, Daniel MT, Ballerni P, Berger R, Fenaux P, Degos L: All-trans retinoic acid as a differentiation therapy for acute promyelocytic leukemia. I. Clinical results. Blood (1990) 76:1704-1709.
74. Warrell RP, Frankel SR, Miller WH, Scheinberg DA, Itri LM, Hittelman WN, Vyas R, Andreeff M, Tafuri A, Jakubowski A, Gabrilove J, Gordon MS, Dmitrovsky E: Differentiation therapy of acute promyelocytic leukemia with all-trans-retinoic acid (tretinoin). New Engl J Med (1991) 324:1385-1393.
75. Frankel SR, Eardley A, Heller G, Berman E, Miller WH, Dmitrovsky E, Warrell Jr RP: All-trans retinoic acid for acute promyelocytic leukemia. Results of the New York Study. Ann Intern Med (1994) 120:278-286.
76. Asuo N, Adachi K, Tamura J, Kanamaru A, Kageyama S, Hiraoka A, Omoto E, Sakamaki H, Tsubaki K, Saito K, Ohno R: All-trans retinoic acid therapy for newly diagonosed acute promyelocytic leukemia: comparison with intensive chemotherapy. The Japan Adult Leukemia Study Group (JALSG). Cancer Chemother Pharmacol (1997) 40(Suppl):S30-35.
77. De Botton S, Dombret H, Sanz M, Miguel JS, Caillot D, Zittoun R, Gardembas M, Stamatoulas A, Condé E, Guerci A, Gardin C, Geiser K, Makhoul DC, Reman O, de la Serna J, Lefrere F, Chomienne C, Chastang C, Degos L, Fenaux P: Incidence, clinical features, and outcome of all trans-retinoic acid syndrome in 413 cases of newly diagnosed acute promyelocytic leukemia. The European APL Group. Blood (1998) 92(8):2712-2718.
78. de Thé H, Chomienne C, Lanotte M, Degos L, Dejean A: The t(15;17) translocation of acute promyelocytic leukaemia fuses the retinoic acid receptor α gene to a novel transcribed locus. Nature (1990) 347(6293):558-561.
79. Biondi A, Rambaldi A, Alcalay M, Pandolfi PP, Coco FL, Diverio D, Rossi V, Mencarelli A, Longo L, Zangrilli D, Masera G, Barbui T, Mandelli F, Grignani F, Pellicci G: RAR-α gene rearrangements as a genetic marker for diagnosis and monitoring in acute promyelocytic leukemia. Blood (1991) 77:1418-1422.
80. Kakizuka A, Miller Jr WH, Umesono K, Warrell Jr RP, Frankel SR, Murty VWS, Dmitrovsky E, Evans RM: Chromosomal Translocation t(15;17) in human acute promyelocytic leukemia fuses rar with a novel putative transcription factor, PML. Cell (1991) 66(4):663-674.
81. Miller Jr WH, Kakizuka A, Frankel SR, Warrell, Jr RP, DeBlasio A, Levine K, Evans RM, Dmitrovsky E: Reverse transcription polymerase chain reaction for the rearranged retinoic acid receptor α clarifies diagnosis and detects minimal residual disease in acute promyelocytic leukemia. Proc Natl Acad Sci USA (1992) 89(7):2694-2698.
82. Kastner P, Perez A, Lutz Y, Rochette-Egly C, Gaub MP, Durand B, Lanotte M, Berger R, Chambon P: Structure, localization and transcriptional properties of two classes of retinoic acid receptor alpha fusion proteins in acute promyelocytic leukemia (APL): structural similarities with a new family of oncoproteins. EMBO J (1992) 11(2):629-642.
83. Redner RL, Rush EA, Faas S, Rudert WA, Corey SJ: The t(5;17) variant of acute promyelocytic leukemia expresses a nucleophosmin-retinoic acid receptor fusion. Blood (1996) 87(3):882-886.
84. Wells RA, Catzavelos C, Kamel-Reid S: Fusion of retinoic acid receptor alpha to NuMA, the nuclear mitotic apparatus protein, by a variant translocation in acute promyelocytic leukaemia. Nature Genet (1997) 17(1):109-113.
85. Lin RJ, Nagy L, Inoue S, Shao W, Miller Jr WH, Evans RM: Role of the histone deacetylase complex in acute promyelocytic leukemia. Nature (1998) 391 (6669):811-814.
86. Grignani F, De Matteis S, Nervi C, Tomassoni L, Gelmetti V, Cioce M, Fanelli M, Ruthardt M, Ferrara FF, Zamir I, Seiser C, Grignani F, Lazar MA, Minucci S, Pelicci PG: Fusion proteins of the retinoic acid receptor-α recruit histone deacetylase in promyelocytic leukemia. Nature (1998) 391(6669):815-818.
87. Jansen JH, de Ridder MC, Geertsma WMC, Erpelinck CAJ, van Lom K, Smit EME, Slater R, vd Reijden BA, de Greef GE, Sonneveld P, Löwenberg B: Complete remission of t(11;17) positive acute promyelocytic leukemia induced by all-trans retinoic acid and granulocyte colony-stimulating factor. Blood (1999) 94(1):39-45.
88. Muindi JR, Frankel SR, Huselton C, DeGrazia F, Garland WA, Young CW, Warrell Jr RP: Clinical pharmacology of oral all-trans retinoic acid in patients with acute promyelocytic leukemia. Cancer Res (1992) 52(8):2138-2142.
89. Comic M, Delva L, Guidez F, Balitrand N, Degos L, Chomienne C: Induction of retinoic acid-binding protein in normal and malignant human myeloid cells by retinoic acid in acute promyelocytic leukemia patients. Cancer Res (1992) 52(12):3329-3334.
90. Tallman MS, Anderson JW, Schiffer CA: All-trans-fetinoic acid in acute promyelocytic leukemia. New Engl J Med (1997) 337:1021-1028.
91. Takeuchi M, Yano T, Omoto E, Takahashi K, Kibata M, Shudo K, Harada M, Ueda R, Ohno R: Relapsed acute promyelocytic leukemia previously treated with all-trans retinoic acid: clinical experience with a new synthetic retinoid, Am-80. Leukemia and Lymphoma (1998) 31(5-6):441-451.
92. Murakami K, Wierzba K, Sano M, Shibata J, Yonekura K, Hashimoto A, Sato K, Yamada Y: TAC-101, a benzoic acid derivative, inhibits liver metastasis of human gastrointestinal cancer and prolongs the life-span. Clin Exp Metastasis (1998) 16(4):323-331.
93. Murakami K, Matsuura T, Sano M, Hashimoto A, Yonekura K, Sakukawa R, Yamada Y, Saiki I: 4-[3,5-Bis(trimethylsilyl)benzamido]benzoic acid (TAC-101) inhibits the intrahepatic spread of hepatocellular carcinoma and prolongs the life-span of tumor-bearing animals. Clin Exp Metastasis (1998) 16(7):633-643.
94. Murakami K, Sakukawa R, Sano M, Hashimoto A, Shibata J, Yamada Y, Saiki I: Inhibition of angiogenesis and intrahepatic growth of colon cancer by TAC-101. Clin Cancer Res (1999) 5:2304-2310
95. Eyrolles L, Kawachi E, Matsushima Y, Nakajima O, Kagechika H, Hashimoto Y, Shudo K: Retinoid antagonists: Molecular design based on the ligand superfamily concept. Med Chem Res (1992) 2:361-367.
96. Kaneko S, Kagechika H, Kawachi E, Hashimoto Y, Shudo K: Retinoid antagonists. Med Chem Res (1991) 1:220-225.
97. Johnson AT, Klein ES, Gillett SJ, Wang L, Song TK, Pino ME, Chandraratna RAS: Synthesis and characterization of a highly potent and effective antagonist of retinoic acid receptors. J Med Chem (1995) 38:4764-4767.
98. Teng M, Duong TT, Johnson AT, Klein ES, Wang L, Khalifa B, Chandraratna RAS: Identification of highly potent retinoic acid receptor α-selective antagonists. J Med Chem (1997) 40(16):2445-2451.
99. Apfel C, Bauer F, Crettaz M, Forni L, Kamber M, Kaufmann F, LeMotte P, Pirson W, Klaus M: A retinoic acid receptor a antagonist selectively counteracts retinoic acid effects. Proc Natl Acad Sci USA (1992) 89(15):7129-7133.
100. Lee MO, Dawson MI, Picard N, Hobbs PD, Pfahl M: A novel class of retinoid antagonists and their mechanism of action. J Biol Chem (1996) 271(20):11897-11903.
101. Yoshimura H, Nagai M, Hibi S, Kikuchi K, Abe S, Hida T, Higashi S, Hishinuma I, Yamanaka TA: Novel type of retinoic acid receptor antagonist: synthesis and structure-activity relationships of heterocyclic ring-containing benzole acid derivatives. J Med Chem (1995) 38:3163-3173.
102. Eyrolles L, Kagechika H, Kawachi E, Fukasawa H, Iijima T, Matsushima Y, Hashimoto Y, Shudo K: Retinobenzoic acids. 6. Retinoid antagonists with a heterocyclic ring. J Med Chem (1994) 37:1508-1517.
103. Klein ES, Pino ME, Johnson AT, Davies PJA, Nagpal S, Thacher SM, Krasinski G, Chandraratna RAS: Identification and functional separation of retinoic acid receptor neutral antagonists and inverse agonists. J Biol Chem (1996) 271(37):22692-22696.
104. Toma S, Isnardi L, Raffo P, Riccardi L, Dastoli G, Apfel C, LeMotte P, Bollag W: RARα antagonist Ro 41-5253 inhibits proliferation and induces apoptosis in breast-cancer cell lines. Int J Cancer (1938) 78(1):86-94.
105. Umemiya H, Fukasawa H, Ebisawa M, Eyrolles L, Kawachi E, Eisenmann G, Gronemeyer H, Hashimoto Y, Shudo K, Kagechika H: Regulation of retinoidal actions by diazepinylbenzoic acids. Retinoid synergists which activate the RXR-RAR heterodimers. J Med Chem (1997) 40(26):4222-4234.
106. Li Y, Hashimoto Y, Agadir A, Kagechika H, Zhang X-K: Identification of a novel class of RARβ-selective retinoid antagonists and their inhibitory effects on AP-1 activity and retinoic acid-induced apoptosis in human breast cancer cells. J Biol Chem (1999) 274(22):15360-15366.
107. Johnson AT, Wang L, Standeven AM, Escobar M, Chandraratna RSA: Synthesis and biological activity of high-affinity retinoic acid receptor antagonists. Bioorg Med Chem (1999) 7(7):1321-1338.
108. Pfahl M: Nuclear receptor/AP-1 interaction. Endocr Rev (1993) 14:651-658.
109. Fanjui A, Dawson MI, Hobbs PD, Jong L, Cameron JF, Harlev E, Graupner G, Lu X-P, Pfahl M: A new class of retinoids with selective inhibition of AP-1 inhibits proliferation. Nature (1994) 372:107-111.
110. Nagpal S, Athanikar J, Chandraratna RAS: Separation of transactivation and AP1 antagonism functions of retinoic acid receptor α. J Biol Chem (1995) 270:923-927.
111. Kagechika H, Kawachi E, Fukasawa H, Saito G, Iwanami N, Umemiya H, Hashimoto Y, Shudo K: Inhibition of IL-1-induced IL-6 production by synthetic retinoids. Biochem Biophys Res Commun (1997) 231(2):243-248.
112. Lehmann JM, Jong L, Fanjui A, Cameron JF, Lu XP, Haefner P, Dawson MI, Pfahl M: Retinoids selective for retinoid X receptor response pathways. Science (1992) 258(5090):1944-1946.
113. Roy B, Taneja R, Chambon P: Synergistic activation of retinoic acid (RA)-responsive genes and induction of embryonal carcinoma cell differentiation by an RA receptor α (RARα)-, RARβ- or RARγ-selective ligand in combination with a retinoid X receptor-specific ligand. Mol Cell Biol (1995) 15:6481-6487.
114. Apfel CM, Kamber M, Klaus M, Mohr P, Keidel S, LeMotte PK: Enhancement of HL-60 differentiation by a new class of retinoids with selective activity on retinoid X receptor. J Biol Chem (1995) 270:30765-30772.
115. Chen JY, Clifford J, Zusi C, Starrett J, Tortolani D, Ostrowski J, Reczek PR, Chambon P: Gronemeyer H: Two distinct actions of retinoid-receptor ligands. Nature (1996) 382(6594):819-822.
116. Umemiya H, Kagechika H, Fukasawa H, Kawachi E, Ebisawa M, Hashimoto Y, Eisenmann G, Erb C, Pomon A, Chambon P, Gronemeyer H, Shudo K: Action mechanism of retinoid-synergistic dibenzodiazepines. Biochem Biophys Res Commun (1997) 233(1):121-125.
117. Minucci S, Leid M, Toyama R, Saint-Jeannet J-P, Peterson VJ, Horn V, Ishmael JE, Bhattacharyya N, Dey A, Dawid IB, Ozato K: Retinoid X receptor (RXR) within the RXR-retinoic acid receptor heterodimer binds its ligand and enhances retinoid-dependent gene expression. Mol Cell Biol (1997) 17(2):644-655.
118. Canan Koch SSC, Dardashti LJ, Hebert JJ, White SK, Croston GE, Flatten KS, Heyman RA, Nadzan AM: Identification of the first retinoid X receptor homodimer antagonist. J Med Chem (1996) 39(17):3229-3234.
119. Lala DS, Mukherjee R, Schulman IG, Koch SS, Dardashti LJ, Nadzan AM, Croston GE, Evans RM, Heyman RA: Activation of specific RXR heterodimers by an antagonist of RXR homodimers. Nature (1996) 383(6599):450-453.
120. Ebisawa M, Umemiya H, Ohta K, Fukasawa H, Kawachi E, Christoffel G, Gronemeyer H, Tsuji M, Hashimoto Y, Shudo K, Kagechika H: Retinoid X receptor-antagonistic diazepinylbenzoic acids. Chem Pharm Bull submitted.
121. Boehm MF, Zhang L, Badea BA, White SK, Mais DE, Berger E, Suto CM, Goldman ME, Heyman RA: Synthesis and structure-activity relationships of novel retinoid X receptor-selective retinoids. J Med Chem (1994) 37:2930-2941.
122. Gottrardis MM, Bischoff ED, Shirley MA, Wagoner MA, Lamph WW, Heyman RA: Chemoprevention of mammary carcinoma by LGD1069 (Targretin): an RXR-selective ligand. Cancer Res (1996) 56(24):5566-5570.
123. Bischoff ED, Gottardis MM, Moon TE, Heyman RA, Lamph WW: Beyond tamoxifen: the retinoid X receptor-selective ligand LGD1069 (Targretin) causes complete regression of mammary carcinoma. Cancer Res (1998) 58(3):479-484.
124. Miller VA, Benedetti FM, Rigas JR, Verret AL, Pfister DG, Straus D, Kris MG, Crisp M: Heyman R, Loewen GR, Truglia JA, Warrell Jr RP: Initial clinical trial of a selective retinoid X receptor ligand, LGD1069. J Clin Oncol (1997) 15(2)790-795.
125. Boehm MF, Zhang L, Zhi L, McClurg MR, Berger E, Wagoner M, Mais DE, Suto CM, Davies PJA, Heyman RA, Nadzan AM: Design and synthesis of potent retinoid X receptor selective ligands that induce apoptosis in leukemia cells. J Med Chem (1995) 38:3146-3155.
126. Lehmann JM, Moore LB, Smith-Oliver TA, Wilkinson WO, Willson TM, Kliewer SA: An antidiabetic thiazolidinedione is a high affinity ligand for peroxisome proliferator-activated receptor γ (PPAR γ). J Biol Chem (1995) 270:12953-12956.
127. Kuwabara K, Shudo K, Hori Y: Novel synthetic retinoic acid inhibits rat collagen arthritis and differentially affects serum immunoglobulin subclass levels. FEBS Lett (1996) 378(2):153-156.
128. Marcellus DC, Altomonte VL, Farmer ER, Horn TD, Freemer CS, Grant J, Vogelsang GB: Etretinate therapy for refractory sclerodermatous chronic graft-versus-host disease. Blood (1999) 93(1):66-70.